Реакция #43918

Уравнение реакции

1,1′-(azodicarbonyl)dipiperidine

methyl[(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate

{4′-[2-(ethylthio)ethoxy]-2′,6′-dimethylbiphenyl-3-yl}methanol

tributylphosphine

→

title compound

Выход 60.0%

Methyl[(3S)-6-({4′-[2-(ethylthio)ethoxy]-2′,6′-dimethylbiphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate

Выход 60.0%

Растворители

Hexane

toluene

Условия реакции

Обработка

1. 1
   Фильтрацияthe precipitated insoluble substance was filtered off
2. 2
   Концентрированиеthe filtrate was concentrated under reduced pressure
3. 3
   ДругоеThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60)

Методика

A solution of methyl[(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate (0.250 g, 1.20 mmol), {4′-[2-(ethylthio)ethoxy]-2′,6′-dimethylbiphenyl-3-yl}methanol (0.380 g, 1.20 mmol) and tributylphosphine (0.388 g, 1.92 mmol) in toluene (20 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.484 g, 1.92 mmol) was added, and the mixture was stirred at room temperature for 1 hr under nitrogen atmosphere. Hexane (10 mL) was added to the reaction mixture, the precipitated insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60) to give the title compound (0.363 g, yield 60%) as a pale-yellow oil.

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